98405-79-9

Basic information

• Product Name: 3-Butenenitrile, 2,2-dimethyl-4-phenyl-, (E)-
• CAS NO: 98405-79-9
• Molecular Formula: C12H13N
• Molecular Weight: 171.242
• Mol File: 98405-79-9.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: 3-Butenenitrile, 2,2-dimethyl-4-phenyl-, (E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Butenenitrile, 2,2-dimethyl-4-phenyl-, (E)-(98405-79-9)
• EPA Substance Registry System: 3-Butenenitrile, 2,2-dimethyl-4-phenyl-, (E)-(98405-79-9)

Safety Data

• Hazardous Substances Data: 98405-79-9(Hazardous Substances Data)

Upstream product

• 78-67-1 2,2'-azobis(isobutyronitrile) 
• 102-96-5 (2-nitroethenyl)benzene 
• 103-64-0 bromostyrene 
• 100-42-5 styrene 
• 536-74-3 phenylacetylene 
• 637-44-5 phenylpropyolic acid 
• 621-82-9 Cinnamic acid 
• 98-02-2 2-thiolomethyl-furan 
• 66680-87-3 (2-phenylvinyl)tributylstannane 
• 2032-35-1 Bromoacetaldehyde diethyl acetal 
• 7677-24-9 trimethylsilyl cyanide 
• 100103-33-1 (E)-(3-methoxy-3-methylbut-1-en-1-yl)benzene 
• 539-74-2 Ethyl 3-bromopropionate 
• 10368-81-7 methyl 4-O-benzoyl-6-bromo-6-deoxy-α-D-glucopyranoside 

Downstream Products

• 15732-83-9 (E)-2,2-dimethyl-4-phenyl-3-buten-1-ol 
• 15732-85-1 2,2-dimethyl-4-phenyl-butan-1-ol 
• 15732-89-5 (E)-2,2-dimethyl-4-phenylbut-3-enoic acid 

Relevant articles and documents

Copper-catalyzed decarboxylative cross-coupling of cinnamic acids and ACCN via single electron transfer

A novel and convenient method for the synthesis of β,γ-unsaturated nitriles using ACCN (1,1′-azobis(cyclohexane-1-carbonitrile)) as a cyano source was described. This reaction was amenable to a broad range of substrates and provided the desired β,γ-unsatu

Selective Synthesis of (E)- and (Z)-Allyl Nitriles via Decarboxylative Reactions of Alkynyl Carboxylic Acids with Azobis(alkylcarbonitriles)

Allyl nitriles were synthesized from the reactions of arylpropiolic acids with azobis(alkylcarbonitriles) (AIBN or ACCN). In the presence of Cu(OAc)2 as a catalyst and pyridine as the solvent, the (E)-stereoisomer was formed as the major product. This transformation shows good tolerance toward alkoxy, halogen, alcohol, amine, ester, and ketone functional groups. When the reaction was conducted with the sterically bulky amine, ethyldiisopropylamine, in the absence of a copper catalyst, the corresponding (Z)-stereoisomers were formed preferentially.

Metal-Free-Catalyzed Synthesis of Allyl Nitriles via Csp2-Csp3 Coupling between Olefins and Azobis (Alkyl-carbonitrile)

The metal-free-catalyzed synthesis of allyl nitriles from Csp2-Csp3 coupling between olefins and azobis was carried out. Key on this work was that the synthesis of allyl nitriles directly using olefin as a start

Synthesis method of (E)-2, 2-dimethyl-4-aryl-butyl-3-enitrile compound

The invention discloses a synthesis method of (E)-2, 2-dimethyl-4-aryl-butyl-3-enitrile compound, and the method comprises the following step: carrying out one-pot reaction on aromatic olefin compounds and AIBN under the catalysis of elemental iodine to obtain the (E)-2, 2-dimethyl-4-aryl-butyl-3-enitrile compounds. The method does not need to adopt a metal catalyst and a toxic solvent, and is beneficial to environmental protection, mild in reaction condition, simple in step, high in target product yield, high in atom utilization rate and beneficial to industrial production.

Reversible Structural Transformations of Metal–Organic Frameworks as Artificial Switchable Catalysts for Dynamic Control of Selectively Cyanation Reaction

The synthesis of molecular-level artificial switchable catalysts, of which activity in different chemical processes can be switched by controlling different stimuli, has provided a new paradigm to perform mechanical tasks and measurable work. In this work, to obtain highly effective and regioselective artificial switchable catalysts, a hierarchical anion-pillared framework {(H3O)[Cu(CPCDC)(4,4′-bpy)]}n (1; H3CPCDC=9-(4-carboxyphenyl)-9H-carbazole-3,6-dicarboxylic acid, 4,4′-bpy=4,4′-bipyridine), including free [H3O]+ ions as guest molecules, was constructed. Upon dissolve–exchange–crystallization behavior, fascinating reversible structural transformations proceeded between anion framework 1 and neutral 2D stair-stepping framework {[Cu(CPCDC)(4,4′-bpe)]}n (2; 4,4′-bpe=4,4′-vinylenedipyridine). Moreover, frameworks 1 and 2 can act as heterogeneous artificial switchable catalysts to selectively promote the direct cyanation reaction of terminal alkynes and azobisisobutyronitrile. The results indicated that 1 and 2 exhibited excellent selectivity to generate vinyl isobutyronitrile skeletons or propiolonitrile frameworks, respectively, as unique products. Furthermore, indicating paper, GC-MS, energy-dispersive X-ray spectroscopy, and X-ray photoelectron spectroscopy analysis demonstrated that the reversible structural transformations endowed 1 and 2 with well-defined platforms to stabilize the isobutyronitrile and CN sources through the different catalytic pathways.

Cu-Catalyzed direct cyanation of terminal alkynes with AMBN or AIBN as the cyanation reagent

A Cu-catalyzed direct cyanation of terminal alkynes was reported with broad substrate generality in moderate to high yield, and AMBN (azobisisoamylonitrile)/AIBN (azobisisobutyronitrile) were used as less toxic and effective cyanating sources in open air. Interestingly, addition products were selectively achieved as the major product under the same conditions in argon.

Photochemical reactivity of 1-substituted-1-aza-1,4-dienes promoted by electron-acceptor sensitizers. Di-π-methane rearrangements and alternative reactions via radical-cation intermediates

Irradiation of a series of β,γ-unsaturated imines, oxime acetates, and oxime methyl ethers, using 9,10-dicyanoanthrathene (DCA) or dicyanodurene (DCD) as electron acceptor sensitizers, affords the corresponding cyclopropanes resulting from 1-aza-di-π-methane rearrangements via radical cations. In some cases, alternative reactions of these intermediates occur to yield nitriles, dihydroquinolines, dihydronaphthalene derivatives, and cycloaddition products. Some of these products result from reactions via alkene radical-cation intermediates while others arise by pathways involving imine radical-cation intermediates. The yields of products formed in these processes were significantly higher when DCD was used as electron-acceptor sensitizer instead of DCA.

Free-Radical Addition of Heteroarenethiols and Heteroarylmethanethiols to Hexyne and Phenylacetylene. Chemical Behavior of the Transient β-Sulfanylvinyl Radicals

The free-radical reaction of a number of heteroarenethiols (including 2-thiophene-, 2-benzofuran-, and 2-benzothiophenethiol) and heteroarylmethanethiols (including 2-furyl-, 2-thienyl-, and 3-thienylmethanethiol) with hex-1-yne and phenylacetylene has been investigated in benzene solution both at 100 deg C in the presence of AIBN and at room temperature in the presence of BEt3/O2.Under both of these conditions the above thiols generally furnished transient 2-sulfanylvinyl radicals through regioselective addition of corresponding sulfanyl radicals to the terminal alkyne carbon, but 2-benzofuranthiol failed to react with either alkyne in the presence of BEt3/O2 and unexpectedely gave 2-(ethylsulfanyl)benzofuran to a significant extent.The produced 2-(2-heteroarylsulfanyl)vinyl radicals largely preffered to undergo intramolecular H-abstraction reaction rather than intramolecular 5-endo cyclization onto the heteroaryl moiety of the 2-sulfanyl substituent.The 2-- and, especially, 2-vinyl radicals, besides H-abstraction, promptly underwent intramolecular 5-exo cyclization to give spiro radicals that interestingly underwent β-scission of their respective C-S and C-O bond resulting in ring cleavage of the original heteroaryl group.The 2-vinyl radicals did not exhibit any similar 5-exo cyclization, but did undergo a 6-endo cyclization to a very slight extent.

A Facile Synthesis of 1,5-Dienes and β,γ-Unsaturated Nitriles via Trityl Perchlorate-Catalyzed Allylation

In the presence of a catalytic amount of trityl perchlorate, secondary and tertiary allyl ethers smoothly react with allylsilanes and silyl cyanide to give the corresponding 1,5-dienes and β,γ-unsaturated nitriles, respectively, in good yields.

Applications of Consecutive Radical Addition-Elimination Reactions in Synthesis

Alkyl radicals add to the tri-n-butylstannyl substituted terminus of several alkenes; elimination of the stannyl radical results in a preparatively useful, carbon-carbon bond forming reaction, under mild and neutral conditions.